A Carbohydrate-Based Total Syntheses of (+)-Pyrenolide D and (−)-4-epi-Pyrenolide D

A Carbohydrate-Based Total Syntheses of (+)-Pyrenolide D and (−)-4-epi-Pyrenolide D

Efficient total syntheses of (+)-pyrenolide D (5) and (−)-4-epi-pyrenolide D (6) have been achieved from a known 5-deoxy-d-xylose derivative 9 in ten steps with 19% overall yield either exclusively as 5 or as pure 5 and 6 in a 3:2 ratio. Key steps involved are one-pot epoxidation–cyclization by Core...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2011-12, Vol.76 (23), p.9835-9840
Hauptverfasser: Thirupathi, Barla, Reddy, P. Purushotam, Mohapatra, Debendra K
Format: Artikel
Sprache:eng
Schlagworte:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Furans - chemical synthesis
Furans - chemistry
Molecular Conformation
Organic chemistry
Preparations and properties
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Efficient total syntheses of (+)-pyrenolide D (5) and (−)-4-epi-pyrenolide D (6) have been achieved from a known 5-deoxy-d-xylose derivative 9 in ten steps with 19% overall yield either exclusively as 5 or as pure 5 and 6 in a 3:2 ratio. Key steps involved are one-pot epoxidation–cyclization by Corey–Chaykvosky reagent, reductive Barton–McCombie deoxygenation, and per-acid mediated oxidative spiroketalization.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo201570h